What is the cheapest airline that flies from Chicago Midway to Milan?

Delta is the most popular carrier operating from Chicago Midway to Milan

When did momondo last update prices for flights from Chicago Midway Airport to Milan?

Prices for flights from Chicago Midway Airport to Milan are updated daily.

How old do you have to be to fly from Chicago Midway Airport to Milan?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Milan.

What documentation or ID do you need to fly to Milan?

The necessary travel and health documents for your Milan trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$300 Cheap Flights from Chicago Midway Airport to Milan in 2025/26

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12:48 pm - 9:05 am

MDW

MXP

13h 17m1 stop

11:05 am - 10:42 pm

MXP

MDW

18h 37m1 stop

$829KLM

Mon, Feb 2 - Wed, Feb 25

1:26 pm - 11:40 am

MDW

MXP

15h 14m2 stops

11:05 am - 10:42 pm

MXP

MDW

18h 37m1 stop

$833Delta

Sun, Feb 8 - Wed, Feb 18

1:31 pm - 9:45 am

MDW

MXP

13h 14m2 stops

11:05 am - 10:42 pm

MXP

MDW

18h 37m1 stop

$834Delta

Wed, Feb 4 - Thu, Feb 12

10:48 am - 9:05 am

MDW

MXP

15h 17m1 stop

11:05 am - 10:42 pm

MXP

MDW

18h 37m1 stop

$879Delta

Fri, Jan 30 - Fri, Feb 13

1:26 pm - 10:35 am

MDW

MXP

14h 09m2 stops

11:05 am - 10:22 pm

MXP

MDW

18h 17m1 stop

$883Delta

Mon, Feb 2 - Mon, Feb 9

10:48 am - 9:45 am

MDW

MXP

15h 57m2 stops

11:05 am - 10:42 pm

MXP

MDW

18h 37m1 stop

$884Delta

Fri, Jan 30 - Fri, Feb 13

10:48 am - 9:05 am

MDW

MXP

15h 17m1 stop

11:05 am - 10:44 pm

MXP

MDW

18h 39m1 stop

$887KLM

Sun, Feb 1 - Tue, Feb 24

1:26 pm - 11:15 am

MDW

LIN

14h 49m2 stops

6:30 am - 5:45 pm

LIN

MDW

18h 15m2 stops

$892Delta

Mon, Feb 9 - Mon, Feb 23

10:46 am - 9:05 am

MDW

MXP

15h 19m1 stop

6:55 am - 4:16 pm

MXP

MDW

16h 21m2 stops

$940Delta

Sat, Jan 31 - Sun, Feb 8

12:48 pm - 9:05 am

MDW

MXP

13h 17m1 stop

11:05 am - 10:42 pm

MXP

MDW

18h 37m1 stop

$954KLM

Sun, Feb 1 - Wed, Feb 25

KLM flights from Chicago Midway Airport to Milan

Our best KLM deals on Chicago Midway Airport to Milan flight tickets

KLM

Feb 2

MDW12:48 pmChicago Midway

13h 17m

1 stop

MXP9:05 amMilan Malpensa

Feb 25

MXP11:05 amMilan Malpensa

18h 37m

1 stop

MDW10:42 pmChicago Midway

$829

Find similar

KLM

Feb 1

MDW10:48 amChicago Midway

15h 17m

1 stop

MXP9:05 amMilan Malpensa

Feb 24

MXP11:05 amMilan Malpensa

18h 39m

1 stop

MDW10:44 pmChicago Midway

$887

Find similar

KLM

Feb 1

MDW12:48 pmChicago Midway

13h 17m

1 stop

MXP9:05 amMilan Malpensa

Feb 25

MXP11:05 amMilan Malpensa

18h 37m

1 stop

MDW10:42 pmChicago Midway

$954

Find similar

Delta flights from Chicago Midway Airport to Milan

Our best Delta deals on Chicago Midway Airport to Milan flight tickets

Delta

Feb 8

MDW1:26 pmChicago Midway

15h 14m

2 stops

MXP11:40 amMilan Malpensa

Feb 18

MXP11:05 amMilan Malpensa

18h 37m

1 stop

MDW10:42 pmChicago Midway

$833

Find similar

Delta

Feb 4

MDW9:32 amChicago Midway

17h 13m

2 stops

MXP9:45 amMilan Malpensa

Feb 13

MXP11:05 amMilan Malpensa

18h 37m

1 stop

MDW10:42 pmChicago Midway

$834

Find similar

Delta

Jan 30

MDW10:48 amChicago Midway

15h 17m

1 stop

MXP9:05 amMilan Malpensa

Feb 13

MXP11:05 amMilan Malpensa

18h 37m

1 stop

MDW10:42 pmChicago Midway

$879

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Milan that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 2/2

12:48 pm-9:05 am

1 stop13h 17m

Milan Malpensa

Wed 2/25

11:05 am-10:42 pm

1 stop18h 37m

$829

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 2/8

1:26 pm-11:40 am

2 stops15h 14m

Milan Malpensa

Wed 2/18

11:05 am-10:42 pm

1 stop18h 37m

$833

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 2/4

1:31 pm-9:45 am

2 stops13h 14m

Milan Malpensa

Thu 2/12

11:05 am-10:42 pm

1 stop18h 37m

$834

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Fri 1/30

10:48 am-9:05 am

1 stop15h 17m

Milan Malpensa

Fri 2/13

11:05 am-10:42 pm

1 stop18h 37m

$879

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 2/2

1:26 pm-10:35 am

2 stops14h 09m

Milan Malpensa

Mon 2/9

11:05 am-10:22 pm

1 stop18h 17m

$883

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Fri 1/30

10:48 am-9:45 am

2 stops15h 57m

Milan Malpensa

Fri 2/13

11:05 am-10:42 pm

1 stop18h 37m

$884

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 2/1

10:48 am-9:05 am

1 stop15h 17m

Milan Malpensa

Tue 2/24

11:05 am-10:44 pm

1 stop18h 39m

$887

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

Mon 2/9

1:26 pm-11:15 am

2 stops14h 49m

Milan Linate

Mon 2/23

6:30 am-5:45 pm

2 stops18h 15m

$892

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sat 1/31

10:46 am-9:05 am

1 stop15h 19m

Milan Malpensa

Sun 2/8

6:55 am-4:16 pm

2 stops16h 21m

$940

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 2/1

12:48 pm-9:05 am

1 stop13h 17m

Milan Malpensa

Wed 2/25

11:05 am-10:42 pm

1 stop18h 37m

$954

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago Midway Airport to Milan

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

What is the cheapest day to depart on your flight to Milan?

Our data shows that Tuesday is the least expensive day to fly to Milan. Tickets to fly out on this day can be as low as $1,183. The most expensive day to fly to Milan is Saturday, with ticket prices averaging around $1,494.

What is the cheapest time of day to depart on your flight to Milan?

In the morning is the cheapest time of day to fly from Chicago Midway Airport to Milan when you can find flight prices for as low as $703. Flying to Milan in the morning is an ideal time because this is during off-peak travel hours. Flights to Milan are more costly in the evening, with an average ticket price of $1,349. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.

Can stopping save me money on Chicago Midway Airport to Milan flights?

You could potentially save up to 2% on your flight if you consider stops on a Chicago Midway Airport to Milan flight.

When to book flights from Chicago Midway Airport to Milan

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Milan according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago Midway Airport to Milan (MDW to MIL) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Milan

Fastest flight time	13h 17m
Direct flights	None

The fastest flight from Chicago Midway Airport to Milan takes 13h 17m

There are no direct flights from Chicago Midway Airport to Milan. There are no popular flight routes from Chicago Midway Airport to Milan.

Search flight deals

How far is Chicago Midway to Milan by plane?
Milan is 4534.8 mi away from Chicago Midway. Flights usually cover this in 12h 20m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Chicago Midway Airport to Milan?
Prices for flights from Chicago Midway Airport to Milan are updated daily.
How old do you have to be to fly from Chicago Midway Airport to Milan?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Milan.
What documentation or ID do you need to fly to Milan?
The necessary travel and health documents for your Milan trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Bellagio

Varenna

Menaggio

Brescia

Stresa

Assago

Levanto

Monza

Livigno

Bellano

Lecco

Domodossola

Bormio

Crema

Rho

Cernobbio

Moltrasio

Saronno

Baveno

Novara

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Milan?

Finding the right flight to Milan from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Milan quick and easy, saving you time and money.

Can I find flights from Chicago to Milan with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Milan from Chicago with this policy.

How can momondo help me find flights from Chicago to Milan?

Once you have performed a search for Chicago to Milan flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Chicago to Milan right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Milan now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Milan and let you know when they change.

An easier way to manage your Milan trip

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Find better results for your trip to Italy

Fly into one of these airports located in Milan

Milan Linate Airport

Milan Malpensa Airport

Cheap flights from Chicago Midway Airport to Milan from $300

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Milan departing on 1/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Chicago Midway Airport to Milan

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

KLM flights from Chicago Midway Airport to Milan

Our best KLM deals on Chicago Midway Airport to Milan flight tickets

Delta flights from Chicago Midway Airport to Milan

Our best Delta deals on Chicago Midway Airport to Milan flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Milan that are best for you.

See travel insights to Milan from

How to get the cheapest flight ticket from Chicago Midway Airport to Milan

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Milan?

Our data shows that Tuesday is the least expensive day to fly to Milan. Tickets to fly out on this day can be as low as $1,183. The most expensive day to fly to Milan is Saturday, with ticket prices averaging around $1,494.

What is the cheapest time of day to depart on your flight to Milan?

Can stopping save me money on Chicago Midway Airport to Milan flights?

You could potentially save up to 2% on your flight if you consider stops on a Chicago Midway Airport to Milan flight.

What is the cheapest airline that flies from Chicago Midway to Milan?

Delta is the most popular carrier operating from Chicago Midway to Milan

When to book flights from Chicago Midway Airport to Milan

Cheap Chicago Midway Airport to Milan (MDW to MIL) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Milan

Fastest flight time

Direct flights

How far is Chicago Midway to Milan by plane?

When did momondo last update prices for flights from Chicago Midway Airport to Milan?

How old do you have to be to fly from Chicago Midway Airport to Milan?

What documentation or ID do you need to fly to Milan?

Traveling to a place near Milan?

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Milan?

Can I find flights from Chicago to Milan with flexible booking policies on momondo?

How can momondo help me find flights from Chicago to Milan?

I’m not ready to book a flight from Chicago to Milan right now. Can momondo alert me if prices change?

An easier way to manage your Milan trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Italy

Fly into one of these airports located in Milan

Airports listed have a maximum distance of 25.0 mi from Milan